Wuweizidilactones A-F: novel highly oxygenated nortriterpenoids with unusual skeletons isolated from Schisandra chinensis.

Chemistry

State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Heilongtan, Kunming 650204, Yunnan, China.

Published: August 2007

A phytochemical study of secondary metabolites produced by Schisandra chinensis has led to the isolation of six novel highly oxygenated nortriterpenoids, wuweizidilactones A-F (1-6). Compounds 3-6 possess an unprecedented 3,4-seco-18(13-->14)-abeo-artane skeleton. Interestingly, structures 3-6 have a beta-oriented methyl group at the C-14 position. This structural feature corroborates the biogenetic pathway proposed for the formation of 18-norschiartane-type compounds 1 and 2. The structures of these novel metabolites were established on the basis of their detailed spectroscopic analysis. The structure of 1 was also confirmed by single-crystal X-ray diffraction analysis. For the first time, the absolute configuration of these nortriterpenoids was determined by using a modified Mosher method.

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http://dx.doi.org/10.1002/chem.200700346DOI Listing

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Wuweizidilactones A-F: novel highly oxygenated nortriterpenoids with unusual skeletons isolated from Schisandra chinensis.

Chemistry

August 2007

State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Heilongtan, Kunming 650204, Yunnan, China.

A phytochemical study of secondary metabolites produced by Schisandra chinensis has led to the isolation of six novel highly oxygenated nortriterpenoids, wuweizidilactones A-F (1-6). Compounds 3-6 possess an unprecedented 3,4-seco-18(13-->14)-abeo-artane skeleton. Interestingly, structures 3-6 have a beta-oriented methyl group at the C-14 position.

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